been to the lizard lounge in cambridge yet? they do all kinds of cool outside jazz and that end of the jam scen there. i saw the slip and the miracle orchestra play all at the same time there.
when i was a kid (growing up outside of boston) i would go to harvard sq. and hear all of the street performers play. this might sound silly except they were people like tracy chapman, martin sexton and G love (garrett in those days). i imagine there are some undescovered singer songwriters sitthing there now who will have big names in a few years. around '90 or so on a given friday or saterday there would be musicians set up on every corner and in every colsed storefront - there would also be swarms of people walking arund listening and behaving like they were at a festi. have you been out there? is it still like this?
......quite a bit of info and i could tell you more....go ahead, mention boston to me and see what happens.....boston is one of my favorite music towns in the world!